[5] From the Arena to the Sales Floor: The Relentless Pursuit of Excellence
I was going through some old boxes the other day when I found them—my competition ribbons from my horseback riding days. Mostly first-place finishes, with a few thirds and fifths sneaking in. Seeing them made me smile, thinking back to just how much ambition and preparation went into every event.
Three-day eventing wasn’t just about showing up and hoping for the best. It was about controlling every variable possible before even stepping into the ring.
Everything had to be dialed in. My horse was groomed for hours, not just to look pristine but to build trust before we performed. Every braid was woven to perfection, because if I was going to do something, I was going to do it right. I would sketch out the entire arena on paper and map my routine with my fingers, rehearsing every movement, every transition, every stride until it felt second nature.
When the moment came, I wasn’t just riding—I was executing on a vision I had already perfected in my mind.
And just like in sales, preparation is everything. You don’t win the deal in the moment—you win it in the prep leading up to the conversation.
But let’s be real: we don’t have hours to sit in deep meditation over every prospect (if you do, let’s talk about your workload). So how do you prepare in a way that’s both time-efficient and highly effective?
1. Know Your Prospect Like You Know Your Horse
Before any competition, I spent hours learning my horse inside and out. What made him nervous? What was his natural pace? Where did I need to adjust my approach to get the best performance? I couldn’t just ride—I had to understand him.
Same goes for sales. You can’t just pitch—you have to understand your prospect.
✅ Their company’s biggest initiatives (check their website, press releases, or LinkedIn posts)
✅ Their role—what problems do they care about? What keeps them up at night?
✅ Their tech stack—are they already using a competitor? Do they have gaps you can solve?
✅ Any personal tidbits that build rapport (mutual connections, shared interests, recent job change)
Pro Tip: Just like I could tell how my horse was feeling with a quick glance, you should be able to gather the most important details about your prospect in five minutes. Skip the deep dive into their college internship and focus on what actually matters.
2. Map Out the Sales Call Like a Course Walk
Before a jumping round, I never just rode into the arena cold. I walked the course, planned every stride, and visualized the perfect ride. I knew where to pick up speed, where to slow down, and exactly how I’d approach each obstacle.
Sales calls should be the same. If you’re just hopping on and winging it, you’re setting yourself up to miss key opportunities. A simple framework:
🚀 Opening: How am I setting the tone? Quick, confident, engaging.
🔎 Discovery: What key questions do I need answered to qualify or move this deal forward?
🎯 Objection Prep: What’s the most common pushback I’ll get, and how will I handle it?
💡 Closing Strategy: What’s my clear next step, and how do I get them to agree to it?
You don’t need a script, but having a structured plan ensures you lead the conversation rather than react to it. Just like in the arena, control the pace, anticipate the turns, and ride the course with confidence.
3. Have Your Value Props Ready, Just Like a Strong Riding Position
In the saddle, confidence comes from being prepared. If I second-guessed my approach to a jump, my horse would feel it and hesitate. If I was firm, balanced, and committed, we sailed over effortlessly.
Same goes for delivering value props in sales. If you hesitate, ramble, or sound unsure, your prospect will pick up on that. Instead, be clear, crisp, and confident in explaining why your solution is a game-changer.
📌 Prepare three impact-driven statements tailored to their industry and role.
📌 Keep them short and punchy. Example:
“Companies like yours use [company] to cut compliance prep time by 60%—that’s months of engineering hours saved.”
“Most of our customers switch from [competitor] because they hit limits in automation—let me show you why.”
“If speed matters, our customers get audit-ready in 50% less time than the industry average.”
Just like in riding, commit to your approach. If you hesitate, you lose momentum. If you’re firm, your prospect follows your lead.
4. Prepare for the Unexpected, Just Like a Spooky Horse
No matter how much I prepared, sometimes my horse would spook at absolutely nothing. A shadow? Terrifying. A gust of wind? Clearly the apocalypse. If I wasn’t ready to adjust, things could go south fast.
Sales calls are no different. You have to prepare for the unexpected. Before every conversation, ask yourself:
⚡ What could go wrong? (Stakeholder no-show? A surprise objection? A competitor mentioned?)
⚡ How do I pivot if that happens?
If I felt my horse hesitate, I didn’t panic—I adjusted, reassured him, and kept moving forward. If your prospect throws an objection, stay calm, handle it smoothly, and take control of the conversation.
The Drive to Push Further
One of my dad’s strongest memories from my riding days wasn’t the ribbons, the wins, or the moments on the podium. It was a competition where I had just finished a major event, nailed my routine, and secured first place. A flawless ride, a clear victory.
He ran over to congratulate me, expecting to see excitement and pride on my face. Instead, I was crying.
Confused, he asked what was wrong.
“I could have done better,” I told him.
That moment stuck with him, or myself, more than any trophy or ribbon ever could. It wasn’t about the recognition—it was about knowing I had more to give.
And let’s be honest—we all check the leaderboard. Some of us (me) check it daily (or hourly if it's EOQ). But real success isn’t just the number next to your name. It’s knowing you did everything possible to set your customer up for success.
Did you go beyond just selling and actually help?
The best sales reps aren’t just focused on recognition. They’re focused on execution, preparation, and delivering value that lasts long after the ink is dry. Because at the end of the day, a leaderboard might recognize your win—but your customer’s success is what truly proves you did your job right.
And if you can help a customer crush their goals and see your name at the top of the leaderboard? That’s the sweet spot.
Want to Level Up? Let’s Talk.
Because I’m all about pushing myself (and others) to that next level, I’m giving away my first 10 one-on-one coaching sessions for FREE.
Yep, zero dollars. Just pure sales strategy, pipeline refining, and deal-closing magic.
DM me if you’re interested—no pressure, no pitch, just real talk and tactics.
And before you ask—yes, this series is called Deals in Heels, but men in flats, sneakers, boots, and even Crocs (no judgment… okay, slight judgment) are more than welcome. Sales is for everyone, and so is getting better at it.
Let’s make some deals happen. 🚀🔥🐎